The synthesis and Diels-Alder reactions of (E)- and (Z)-1-methoxy-3-(phenylsulfinyl)-1,3-butadienes

Harry Adams, James C. Anderson, Richard Bell, D. Neville Jones, Michael R. Peel, Nicholas C. O. Tomkinson

Research output: Contribution to journalArticle

Abstract

The mild and efficient generation of benzenesulfenic acid by the thermolysis of Et 2-ethoxycarbonyl-3-(phenylsulfinyl)butanoate in refluxing dichloromethane, its in situ trapping with (E)- and (Z)-1-methoxy-2-buten-3-yne to form (E)-1-methoxy-3-(phenylsulfinyl)-1,3-butadiene and (Z)-1-methoxy-3-(phenylsulfinyl)-1,3-butadienes resp. proceeds in high yield. The lithium perchlorate catalyzed Diels-Alder reaction of (E)-1-methoxy-3-(phenylsulfinyl)-1,3-butadiene with both sym. and unsym. carbonyl activated dienophiles proceeds with complete regioselectivity and in some cases complete endo-selectivity.
Original languageUndefined/Unknown
Pages (from-to)3967-3974
Number of pages8
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number23
Publication statusPublished - 1998

Keywords

  • Diels-Alder reactions
  • 3-butadienes
  • benzenesulfenic acid
  • regioselectivity

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